The literary canon and the Roanoke LGBT Memorial Library are both severely lacking in books by or about transgender and genderqueer people. However, a few books that can be defined in this category are listed below. It is also important to note that the Library's current cataloging system, which divides fiction into "FG" (fiction -- gay) and "FL" (fiction -- lesbian) is problematic for categorizing transgender books.

In this fantastical novel inspired by Woolf's lover Vita Sackville-West, the nobleman Orlando is born a boy before magically becoming a woman later in life. Orlando lives for centuries in both gender roles, taking lovers of all genders and participating in world events.

This novel tells the story of Jess Goldberg's attempts to find a place for herself in society. Not entirely comfortable as a stone butch in lesbian culture, she considers whether she might be a man and want to take testosterone.

This novel tells a fictionalized version of the story of Lili Elbe, the first person to undergo gender confirmation surgery. Lili begins to discover her gender identity through modeling as a woman for her wife's art. This book has been made into an acclaimed film.